ChemInform Abstract: Synthesis of Salts of Heterocyclic N‐ and C‐Nitramino‐N‐nitroimides.

Abstract

Synthesis of Salts of Heterocyclic N-and C-Nitramino-N-nitroimides. -The representative (III) of the title compounds is prepared by amination of the aminotriazole (I) with O-picrylhydroxylamine to give the quaternary N-amino compound (II) which is subsequently subjected to nitration. The salts (IV) -(VI) are synthesized in an analogous manner. -(MYASNIKOV, V. A.; VYAZKOV, V. A.; YUDIN, I. L.; SHITOV, O. P.; TARTAKOVSKII, V. A.; Izv.

1,3-Bis(nitroimido)-1,2,3-triazolate Anion, the N-Nitroimide Moiety, and the Strategy of Alternating Positive and Negative Charges in the Design of Energetic Materials

“…This is best exemplified by the fully unsaturated 1,2,3,4-tetrazine ring; without ring nitrogen atoms substitution, it is unstable, with only one low-decomposing example of one such compound existing. , In the case of the 1,2,3,4-tetrazine-1-oxides, an increase in stability is seen with many benzo-annulated species known . The major increase in stability is seen with the 1,2,3,4-tetrazine-1,3-dioxides; generally, members of this class of compounds decompose above 200 °C. − This increase in stability can be described by the above separation of σ and π systems; however, qualitatively it gives rise to the unique “alternating positive negative charge” (APNC) theory, whereby stable nitrogen-rich systems can have one of their resonance forms illustrated with positive and negative charges on alternating atoms. , Unique nitrogen–oxygen systems, beyond 1,2,3,4-tetrazine-1,3-dioxides, can all have their resonance forms illustrated in the APNC form including the nitroimide , and nitrodiazine oxide , functionalities (Figure ). When it is considered that heterocycle stabilization by an oxide results from removal of electron density on alternating nitrogen atoms, there is the potential for heterocycle stabilization by the nitroimide functionality, where extended APNC systems can be created.…”